methyl (S)-2-[(S)-1-(tert-butoxycarbonylamino)ethyl]-4,5-dihydrooxazole-4-carboxylate | 170455-11-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (S)-2-[(S)-1-(tert-butoxycarbonylamino)ethyl]-4,5-dihydrooxazole-4-carboxylate
• 英文别名: methyl (S,S)-2-[1-(((tert-butoxy)carbonyl)amino)eth-1-yl]-1,3-oxazoline-4-carboxylate；Boc-L-Ala-L-Ozn-4-COOMe；methyl (4S)-2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 170455-11-5
• 化学式: C₁₂H₂₀N₂O₅
• 分子量: 272.301
• InChiKey: LXBRHNNGXZRARL-YUMQZZPRSA-N

物化性质

• 沸点：
  365.9±37.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  86.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-[(S)-1-(tert-butoxycarbonylamino)ethyl]-4,5-dihydrooxazole-4-carboxylate 在 吡啶 、 盐酸 、 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  Synthesis of backbone modified cyclic peptides bearing dipicolylamino sidearms

  摘要：

  Three analogues of the Lissoclinum class of cyclic peptides, bearing dipicolylamino functionalised side chains, have been synthesised using a stepwise approach followed by macrocyclisation. Attempts to incorporate dipicolylamino functionalised side chains prior to peptide synthesis resulted in epimerisation, but this was overcome by functionalising the ornithine side chains with dipicolylamino groups after the macrocyclisation reaction. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.100
• 作为产物：
  描述：

  Boc-L-Ala-L-Ser-OMe 在 potassium carbonate 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到methyl (S)-2-[(S)-1-(tert-butoxycarbonylamino)ethyl]-4,5-dihydrooxazole-4-carboxylate
  参考文献：
  名称：

  用DAST和Deoxo-Fluor合成功能化的恶唑啉和恶唑。

  摘要：

  [公式：见正文]使用DAST和Deoxo-Fluor试剂描述了将β-羟基酰胺温和高效环化为恶唑啉的方法。还提出了一种由一锅法从β-羟基酰胺合成恶唑的方案。

  DOI：

  10.1021/ol005777b

文献信息

• Unified Azoline and Azole Syntheses by Optimized Aza-Wittig Chemistry
  作者：Patrick Loos、Cyril Ronco、Matthias Riedrich、Hans-Dieter Arndt

  DOI：10.1002/ejoc.201300160

  日期：2013.6

  Intramolecular aza-Wittig ring closures were applied to synthesize thiazolines, oxazolines, and imidazolines from β-azido thioester, ester, and amide precursors. The cyclization precursors were obtained from amino acid derivatives. Optimized conditions for diazo transfer with a fast rate and racemization suppression, (thio)esterification, and amide coupling reactions are described. The ring closure reaction can

  分子内 aza-Wittig 环闭合用于从 β-叠氮基硫酯、酯和酰胺前体合成噻唑啉、恶唑啉和咪唑啉。环化前体是从氨基酸衍生物中获得的。描述了具有快速和外消旋化抑制、（硫代）酯化和酰胺偶联反应的重氮转移的优化条件。闭环反应可以在中性条件下用 PPh3 进行，并且发现对五元环具有高度的化学选择性。如果酰胺基团被甲苯磺酰基激活，则亚氨基膦的分子内闭环会提供具有位置特异性甲苯磺酰基保护的对映纯咪唑啉产品。
• Peptide-Embedded Heterocycles by Mild Single and Multiple Aza-Wittig Ring Closures
  作者：Matthias Riedrich、Surendra Harkal、Hans-Dieter Arndt

  DOI：10.1002/anie.200604507

  日期：2007.4.2
• Stereochemistry and Total Synthesis of Dolastatin E
  作者：M Nakamura

  DOI：10.1016/00404-0399(50)0923z-

  日期：1995.7.10

  The absolute stereochemistry of dolastatin E (1), a cyclic hexapeptide isolated from the sea hare Dolabella auricularia, has been determined by a combination of the degradation experiments and total synthesis.
• Synthesis and Antimicrobial Activity <i>in Vitro</i> of New Amino Acids and Peptides Containing Thiazole and Oxazole Moieties
  作者：Mincho Stanchev、Svoboda Tabakova、Georgi Videnov、Evgeny Golovinsky、Guenther Jung

  DOI：10.1002/(sici)1521-4184(19999)332:9<297::aid-ardp297>3.0.co;2-#

  日期：1999.9

  2-(Pyrrolidinyl)thiazole-4-carboxylic acid 5d, 2-(1-aminoalkyl)thiazole-4-carboxamides and hydrazides 8, 10 have been synthesized using alanine, valine, and proline as educts. In addition oxazole amino acids derived from leucine 20a and alanine 20b and some peptides 13, 14, 16 containing the 5-ring heterocyclic backbone modifications have been prepared. The thiazole and oxazole containing amino acids and peptides showed moderate antibacterial activity in vitro against various Gram-positive (Staphylococcus aureus, Bacillus cereus, etc.) and Gram-negative (Escherichia coli, Proteus vulgar is, etc.) bacteria, fungi (Candida albicans), and yeast (Saccharomyces cerevisae, etc.).